diff --git a/.github/workflows/ports_windows.yml b/.github/workflows/ports_windows.yml
index 4b1f4ea791e2..6858a146c42d 100644
--- a/.github/workflows/ports_windows.yml
+++ b/.github/workflows/ports_windows.yml
@@ -18,7 +18,132 @@ concurrency:
   cancel-in-progress: true
 
 jobs:
-  build:
+  build-vs:
+    strategy:
+      fail-fast: false
+      matrix:
+        platform: [x86, x64]
+        configuration: [Debug, Release]
+        variant: [dev, standard]
+        visualstudio: ['2017', '2019', '2022']
+        include:
+        - visualstudio: '2017'
+          runner: windows-latest
+          vs_version: '[15, 16)'
+        - visualstudio: '2019'
+          runner: windows-2019
+          vs_version: '[16, 17)'
+        - visualstudio: '2022'
+          runner: windows-2022
+          vs_version: '[17, 18)'
+        # trim down the number of jobs in the matrix
+        exclude:
+        - variant: standard
+          configuration: Debug
+        - visualstudio: '2019'
+          configuration: Debug
+    runs-on: ${{ matrix.runner }}
+    steps:
+    - name: Install Visual Studio 2017
+      if: matrix.visualstudio == '2017'
+      run: |
+        choco install visualstudio2017buildtools
+        choco install visualstudio2017-workload-vctools
+        choco install windows-sdk-8.1
+    - uses: microsoft/setup-msbuild@v1
+      with:
+        vs-version: ${{ matrix.vs_version }}
+    - uses: actions/setup-python@v4
+      if: matrix.runner == 'windows-2019'
+      with:
+        python-version: '3.9' 
+    - uses: actions/checkout@v3
+    - name: Build mpy-cross.exe
+      run: msbuild mpy-cross\mpy-cross.vcxproj -maxcpucount -property:Configuration=${{ matrix.configuration }} -property:Platform=${{ matrix.platform }}
+    - name: Build micropython.exe
+      run: msbuild ports\windows\micropython.vcxproj -maxcpucount -property:Configuration=${{ matrix.configuration }} -property:Platform=${{ matrix.platform }} -property:PyVariant=${{ matrix.variant }} 
+    - name: Get micropython.exe path
+      id: get_path
+      run: |
+        $exePath="$(msbuild ports\windows\micropython.vcxproj -nologo -v:m -t:ShowTargetPath -property:Configuration=${{ matrix.configuration }} -property:Platform=${{ matrix.platform }} -property:PyVariant=${{ matrix.variant }})"
+        echo ("micropython=" + $exePath.Trim()) >> $env:GITHUB_OUTPUT
+    - name: Run tests
+      id: test
+      env:
+        MICROPY_MICROPYTHON: ${{ steps.get_path.outputs.micropython }}
+      working-directory: tests
+      run: python run-tests.py
+    - name: Print failures
+      if: failure() && steps.test.conclusion == 'failure'
+      working-directory: tests
+      run: python run-tests.py --print-failures
+    - name: Run mpy tests
+      id: test_mpy
+      env:
+        MICROPY_MICROPYTHON: ${{ steps.get_path.outputs.micropython }}
+      working-directory: tests
+      run: python run-tests.py --via-mpy -d basics float micropython
+    - name: Print mpy failures
+      if: failure() && steps.test_mpy.conclusion == 'failure'
+      working-directory: tests
+      run: python run-tests.py --print-failures
+
+  build-mingw:
+    strategy:
+      fail-fast: false
+      matrix:
+        variant: [dev, standard]
+        sys: [mingw32, mingw64]
+        include:
+          - sys: mingw32
+            env: i686
+          - sys: mingw64
+            env: x86_64
+    runs-on: windows-2022
+    env:
+      CHERE_INVOKING: enabled_from_arguments
+    defaults:
+      run:
+        shell: msys2 {0}
+    steps:
+    - name: Get Python path
+      id: python_path
+      shell: python
+      run: |
+        import os
+        import sys
+        output = f"python={os.fspath(sys.executable)}"
+        print(output)
+        with open(os.environ["GITHUB_OUTPUT"], "w") as f:
+            f.write(output)
+    - uses: msys2/setup-msys2@v2
+      with:
+        msystem: ${{ matrix.sys }}
+        update: true
+        install: >-
+          make 
+          mingw-w64-${{ matrix.env }}-gcc
+          pkg-config
+          python3
+          git
+          diffutils
+    - uses: actions/checkout@v3
+    - name: Build mpy-cross.exe
+      run: make -C mpy-cross -j2
+    - name: Update submodules
+      run: make -C ports/windows VARIANT=${{ matrix.variant }} submodules
+    - name: Build micropython.exe
+      run: make -C ports/windows -j2 VARIANT=${{ matrix.variant }}
+    - name: Run tests
+      id: test
+      # msys python breaks tests so we need to use "real" windows python
+      run: MICROPY_CPYTHON3=$(cygpath "${{ steps.python_path.outputs.python }}") make -C ports/windows test_full VARIANT=${{ matrix.variant }}
+    - name: Print failures
+      if: failure() && steps.test.conclusion == 'failure'
+      working-directory: tests
+      run: python run-tests.py --print-failures
+
+  cross-build-on-linux:
     runs-on: ubuntu-latest
     steps:
     - uses: actions/checkout@v4
diff --git a/ports/windows/.appveyor.yml b/ports/windows/.appveyor.yml
deleted file mode 100644
index c1a114a0f897..000000000000
--- a/ports/windows/.appveyor.yml
+++ /dev/null
@@ -1,90 +0,0 @@
-image: Visual Studio 2017
-clone_depth: 1
-skip_tags: true
-
-environment:
-  # Python version used
-  MICROPY_CPYTHON3: c:/python38/python.exe
-  # The variants.
-  matrix:
-    - PyVariant: dev
-    - PyVariant: standard
-
-init:
-  # Set build version number to commit to be travis-like
-- ps: Update-AppveyorBuild -Version $env:appveyor_repo_commit.substring(0,8)
-
-configuration:
-- Debug
-- Release
-
-platform:
-- x86
-- x64
-
-matrix:
-  # One debug build is enough.
-  exclude:
-    - configuration: Debug
-      PyVariant: dev
-
-before_build:
-- ps: |
-    @"
-    <?xml version="1.0" encoding="utf-8"?>
-    <Project ToolsVersion="4.0" xmlns="http://schemas.microsoft.com/developer/msbuild/2003">
-      <Target Name="Build">
-        <MsBuild Projects="mpy-cross\mpy-cross.vcxproj;ports\windows\micropython.vcxproj"/>
-      </Target>
-    </Project>
-    "@ | Set-Content build.proj
-
-build:
-  project: build.proj
-  parallel: true
-  verbosity: normal
-
-test_script:
-- ps: |
-    $env:MICROPY_MICROPYTHON=(msbuild ports\windows\micropython.vcxproj /nologo /v:m /t:ShowTargetPath).Trim()
-    cd (Join-Path $env:APPVEYOR_BUILD_FOLDER 'tests')
-    & $env:MICROPY_CPYTHON3 run-tests.py
-    if ($LASTEXITCODE -ne 0) {
-      & $env:MICROPY_CPYTHON3 run-tests.py --print-failures
-      throw "Test failure"
-    }
-    & $env:MICROPY_CPYTHON3 run-tests.py --via-mpy -d basics float micropython
-    if ($LASTEXITCODE -ne 0) {
-      & $env:MICROPY_CPYTHON3 run-tests.py --print-failures
-      throw "Test failure"
-    }
-
-# After the build/test phase for the MSVC build completes,
-# build and test with mingw-w64, release versions only.
-after_test:
-- ps: |
-    if ($env:configuration -eq 'Debug') {
-      return
-    }
-    $env:MSYSTEM = if ($platform -eq 'x86') {'MINGW32'} else {'MINGW64'}
-    $env:CHERE_INVOKING = 'enabled_from_arguments'
-    cd (Join-Path $env:APPVEYOR_BUILD_FOLDER 'mpy-cross')
-    C:\msys64\usr\bin\bash.exe -l -c "make -B -j4 V=1"
-    if ($LASTEXITCODE -ne 0) {
-      throw "$env:MSYSTEM mpy_cross build exited with code $LASTEXITCODE"
-    }
-    cd (Join-Path $env:APPVEYOR_BUILD_FOLDER 'ports/windows')
-    C:\msys64\usr\bin\bash.exe -l -c "make -B VARIANT=$($env:PyVariant) submodules"
-    if ($LASTEXITCODE -ne 0) {
-      throw "$env:MSYSTEM build exited with code $LASTEXITCODE"
-    }
-    C:\msys64\usr\bin\bash.exe -l -c "make -B -j4 V=1 MICROPY_MPYCROSS=../../mpy-cross/build/mpy-cross.exe VARIANT=$($env:PyVariant)"
-    if ($LASTEXITCODE -ne 0) {
-      throw "$env:MSYSTEM build exited with code $LASTEXITCODE"
-    }
-    C:\msys64\usr\bin\bash.exe -l -c "make V=1 test_full VARIANT=$($env:PyVariant)"
-    if ($LASTEXITCODE -ne 0) {
-      cd (Join-Path $env:APPVEYOR_BUILD_FOLDER 'tests')
-      & $env:MICROPY_CPYTHON3 run-tests.py --print-failures
-      throw "Test failure"
-    }
diff --git a/tests/run-tests.py b/tests/run-tests.py
index ecd49a7d75fe..c912f9d5424d 100755
--- a/tests/run-tests.py
+++ b/tests/run-tests.py
@@ -532,6 +532,14 @@ def run_tests(pyb, tests, args, result_dir, num_threads=1):
     if os.getenv("GITHUB_ACTIONS") == "true":
         skip_tests.add("thread/stress_schedule.py")  # has reliability issues
 
+        if os.getenv("RUNNER_OS") == "Windows":
+            # fails with stack overflow on Debug builds
+            skip_tests.add("misc/sys_settrace_features.py")
+
+            if os.getenv("MSYSTEM") is not None:
+                # fails due to wrong path separator
+                skip_tests.add("import/import_file.py")
+
     if upy_float_precision == 0:
         skip_tests.add("extmod/uctypes_le_float.py")
         skip_tests.add("extmod/uctypes_native_float.py")